Pyridine → 3-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl ester

HRID 226123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226123
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:7]=1.[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:14])(=[O:13])[N:18]([CH3:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7515N-MethylanilineHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

Produkt 1

HCID 670195883-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl esterAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (0.440 g, 1.68 mmol) in dichloromethane (2 ml) was added to a mixture of N-methylaniline (0.364 g, 3.40 mmol) and pyridine (0.5 ml), and the resultant solution was stirred at 50° C. for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 10% HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with chloroform-ethyl acetate (15:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.155 g, 28%). 1H NMR (CDCl3, HMDSO), δ: 3.12 (3H, s); 3.74 (3H, s); 6.34 (1H, d, J=16.0 Hz); 6.97-7.74 (10H, m).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 10% HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (15:1
  7. washThe obtained product was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9586c8ea5b3844749616f4dbba056a16
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557140B2

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